4-bromo-2,2-bis(fluoromethyl)-6-nitro-2H-1-benzopyran | 155048-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-bromo-2,2-bis(fluoromethyl)-6-nitro-2H-1-benzopyran
• 英文别名: 4-Bromo-2,2-bis(fluoromethyl)-6-nitrochromene
• CAS: 155048-60-5
• 化学式: C₁₁H₈BrF₂NO₃
• 分子量: 320.09
• InChiKey: RJJVUABCPVLVIC-UHFFFAOYSA-N

物化性质

• 沸点：
  426.2±45.0 °C(Predicted)
• 密度：
  1.631±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-bromo-2,2-bis(fluoromethyl)-6-nitro-2H-1-benzopyran 在 palladium diacetate 、 Raney Ni (W-1) 氢氧化钾 、 copper(l) iodide 、 硫酸 、 氢气 、 potassium acetate 、 三苯基膦 、 N,N'-羰基二咪唑 、 potassium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 2,2-bis(fluoromethyl)-N-methylchromene-4-carboxamide
  参考文献：
  名称：

  6-Substituted 2,2-Bis(fluoromethyl)-benzopyran-4-carboxamide K + channel openers

  摘要：

  In the course of our study to find an ideal antihypertensive potassium channel opener (KCO), N-(2-cyanoethyl)-2,2 bis(fluoromethyl)-6-pentafluoroethyl-2H-1-benzopyran-4-carboxamide (13f, KC-515) showed a highly potent, slow and long-lasting antihypertensive effect with reduced reflex tachycardia, together with the beneficial effects of KCO such as improvement in lipid metabolism. These profiles identify KC-515 as a potential candidate. In conscious spontaneously hypertensive rats (SHR), the onset of the hypotensive effect of KC-515 (13f) was gradual and the maximum response was attained at around 6 h after dosing. The duration of action was over 18 h for 0.1 mg/kg. When administered to Zucker rats for 2 weeks with 0.03-0.3 mg/kg po range in the antihypertensive doses in hypertensive rat models, KC-515 (13f) significantly and dose-dependently reduced serum triglycerides to less than 70% of control without affecting total cholesterol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00064-x
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.5h， 以119.2 g的产率得到4-bromo-2,2-bis(fluoromethyl)-6-nitro-2H-1-benzopyran
  参考文献：
  名称：

  6-Substituted 2,2-Bis(fluoromethyl)-benzopyran-4-carboxamide K + channel openers

  摘要：

  In the course of our study to find an ideal antihypertensive potassium channel opener (KCO), N-(2-cyanoethyl)-2,2 bis(fluoromethyl)-6-pentafluoroethyl-2H-1-benzopyran-4-carboxamide (13f, KC-515) showed a highly potent, slow and long-lasting antihypertensive effect with reduced reflex tachycardia, together with the beneficial effects of KCO such as improvement in lipid metabolism. These profiles identify KC-515 as a potential candidate. In conscious spontaneously hypertensive rats (SHR), the onset of the hypotensive effect of KC-515 (13f) was gradual and the maximum response was attained at around 6 h after dosing. The duration of action was over 18 h for 0.1 mg/kg. When administered to Zucker rats for 2 weeks with 0.03-0.3 mg/kg po range in the antihypertensive doses in hypertensive rat models, KC-515 (13f) significantly and dose-dependently reduced serum triglycerides to less than 70% of control without affecting total cholesterol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00064-x

文献信息

• Synthesis of key intermedia tes benzopyran-4-carboxylic acids of new potassium channel openers benzopyran-4-amides via palladium-catalyzed hydroxycarbonylation
  作者：Hiroshi Koga、Haruhiko Sato、Takenori Ishizawa、Naoki Taka、Tadakatsu Takahashi

  DOI：10.1016/0040-4039(94)02172-8

  日期：1995.1

  Key intermediates benzopyran-4-carboxylic acids of an important class of potassium channel openers benzopyran-4-amides have been synthesized via palladium-catalyzed hydroxycarbonylation.

  一类重要的钾通道开放剂的关键中间体苯并吡喃-4-羧酸是通过钯催化的羟羰基化反应合成的。
• Takahashi, Tadakatsu; Koga, Hiroshi; Sato, Haruhiko, Heterocycles, 1995, vol. 41, # 11, p. 2405 - 2408
  作者：Takahashi, Tadakatsu、Koga, Hiroshi、Sato, Haruhiko、Ishizawa, Takenori、Taka, Naoki

  DOI：——

  日期：——
• Synthesis of Benzopyran-4-Amides Potassium Channel Openers Via Palladium-Catalyzed Amidation
  作者：Naoki Taka、Hiroshi Koga、Haruhiko Sato、Takenori Ishizawa、Tadakatsu Takahashi

  DOI：10.1080/00397910008087048

  日期：2000.12

  The novel potassium channel openers benzopyran-4-amides have been synthesized via palladium-catalyzed amidation of 4-bromobenzopyrans under an atmoshere in the presence of an equivalent of potassium iodide.